Dimethylformamide → HCID 178526784, compound

HRID 711941Notes

Reaction equation

HRID 711941 reaction equation
[N+:1]([C:4]1[C:5]([NH:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([NH2:20])[CH2:16][CH2:15]2)=[C:6]2[S:12][CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2].C(N(CC)C(C)C)(C)C.CN(C)C=O.FC(F)(F)S(O[CH2:41][C:42]([F:45])([F:44])[F:43])(=O)=O>C(Cl)Cl.O>[N+:1]([C:4]1[C:5]([NH:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([NH:20][CH2:41][C:42]([F:45])([F:44])[F:43])[CH2:16][CH2:15]2)=[C:6]2[S:12][CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 81531DiisopropylethylamineHCID 178511653HCID 178511653, compound

Product 1

HCID 178526784HCID 178526784, compoundYield 22.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of trans-N-(6-nitrothieno[3,2-b]pyridin-7-yl)cyclohexane-1,4-diamine (120 mg, 0.41 mmol) and N,N-diisopropylethylamine (0.36 mL, 2.0 mmol) in methylene chloride (2 mL)/N,N-dimethylformamide (2 mL) was added 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.18 mL, 1.2 mmol). The reaction was stirred at room temperature for 4 h. The resulting mixture was diluted with water, extracted with dichloromethane. The organic layers were concentrated and purified on silica gel (eluting with 0 to 5% MeOH in dichloromethane) to give the desired product (34 mg, 22%). LCMS calculated for C15H18F3N4O2S (M+H)+: m/z=375.1. Found: 375.0.

Workup

  1. extractionextracted with dichloromethane
  2. concentrationThe organic layers were concentrated
  3. custompurified on silica gel (eluting with 0 to 5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-b08aff001b1345998fdd2f05872b5570
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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